2-नेफ्थोल

2-नेफ्थोल , या β-नेफ्थोल , एक फ्लोरोसेंट रंगहीन

(या कभी-कभी पीला) क्रिस्टलीय ठोस है जिसका सूत्र C
H OH है। यह 1-नेफ्थोल का एक आइसोमर है,
10 7
जो नेफ़थलीन रिंग पर हाइड्रॉक्सिल समूह के स्थान से
भिन्न होता है । नैफ्थोल फिनोल के नेफ़थलीन समरूप हैं
, लेकिन अधिक प्रतिक्रियाशील हैं। दोनों आइसोमर्स
साधारण अल्कोहल , ईथर और क्लोरोफॉर्म में
घुलनशील हैं । 2-नेफ्थोल रंगों और अन्य यौगिकों के
उत्पादन के लिए व्यापक रूप से इस्तेमाल किया जाने
वाला मध्यवर्ती है ।
 2-नेफ्थोल

नाम
पसंदीदा IUPAC नाम
नेफ़थलीन-2-ओएल
अन्य नामों
2- हाइड्रोक्सीनाफ्थालीन; 2- नेफ़थलेनॉल; बीटा
- नेफ्थोल; नेफ्थ-2- ओएल

पहचानकर्ता
सीएएस संख्या 135-19-3 (https://com
monchemistry.cas.or
g/detail?cas_rn=135-1
9-3)

3डी मॉडल ( इंटरएक्टिव छवि (https://

जेएसएमओएल ) chemapps.stolaf.edu/
jmol/jmol.php?model=
Oc2ccc1c%28cccc1%
29c2)
इंटरएक्टिव छवि (https://
chemapps.stolaf.edu/
jmol/jmol.php?model=
c1ccc2cc%28ccc2c1%
29O)

बेलस्टीन संदर्भ 742134

चेबी चेबी: 10432 (https://w
ww.ebi.ac.uk/chebi/se
archId.do?chebiId=10
432)

ChEMBL सीईएमबीएल14126 (http

s://www.ebi.ac.uk/che
mbldb/index.php/com
pound/inspect/ChEM
BL14126)

के मस्पाइडर 8341 (https://www.ch

emspider.com/Chemic
al-Structure.8341.htm
l)

ईसीएचए इन्फोकार्ड 100.004.712 (https://

echa.europa.eu/subst
ance-information/-/su
 bstanceinfo/100.004.
712)

ईसी संख्या 205-182-7

गमेलिन संदर्भ 27395

के ईजीजी C11713 (https://www.

kegg.jp/entry/C1171
3)

पबके म सीआईडी 8663 (https://pubche

m.ncbi.nlm.nih.gov/co
mpound/8663)

आरटीईसीएस नंबर QL2975000

यूएनआईआई P2Z71CIK5H (https://

precision.fda.gov/unii
search/srs/unii/P2Z7
1CIK5H)
संयुक्त राष्ट्र संख्या 3077

कॉम्पटॉक्स डैशबोर्ड ( डीटीएक्सएसआईडी5027061

ईपीए ) (https://comptox.epa.go
v/dashboard/chemical/d
etails/DTXSID502706
1)

इंची
InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)
7-10/h1-7,11H
कुं जी: ज्वाज़्रिहिनिरिहिव-उहफ्फाओयसा-एन
InChI=1/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7
-10/h1-7,11H
कुं जी: ज्वाज़रिहिनिरिहिव-उहफ्फाओयाव
मुस्कान
ओसी2सीसीसी1सी(सीसीसीसी1)सी2
सी1सीसीसी2सीसी(सीसीसी2सी1)ओ
गुण
रासायनिक सूत्र सी 10 एच 8 ओ
दाढ़ जन 144.173 g·mol−1

Appearance Colorless crystalline

solid

Density 1.280 g/cm3

Melting point 121 to 123 °C (250 to

253 °F; 394 to 396 K)

Boiling point 285 °C (545 °F; 558 K)

Solubility in water 0.74 g/L

Acidity (pKa) 9.51

Magnetic -98.25·10−6 cm3/mol

susceptibility (χ)

Hazards

Occupational safety and health (OHS/OSH):

 Main hazards Harmful when
inhaled or swallowed;
dangerous to
environment, esp.
aquatic organisms.[1]

GHS labelling:

Pictograms

Signal word Warning

Hazard statements H302, H332, H400

Precautionary P261, P264, P270,

statements
P271, P273,
P301+P312,
P304+P312,
P304+P340, P312,
P330, P391, P501
NFPA 704 1
2 0
(fire diamond)

Flash point 161 °C (322 °F;

434 K)[1]

Except where otherwise noted, data are given

for materials in their standard state (at 25 °C
[77 °F], 100 kPa).
verify (https://en.wikipedia.org/w/index.php?
title=Special:ComparePages&rev1=47721474
6&page2=2-Naphthol) (what is ?)
Infobox references

Production
Traditionally, 2-naphthol is produced by a
two-step process that begins with the
sulfonation of naphthalene in sulfuric
acid:[2]

C10H8 + H2SO4 → C10H7SO3H + H2O

The sulfonic acid group is then cleaved in

molten sodium hydroxide:

C10H7(SO3H) + 3 NaOH → C10H7ONa +

Na2SO3 + 2 H2O

Neutralization of the product with acid

gives 2-naphthol.

2-Naphthol can also be produced by a

method analogous to the cumene
process.[2]
2-Naphthol-derived dyes
The Sudan dyes are popular dyes noted
for being soluble in organic solvents.
Several of the Sudan dyes are derived from
2-naphthol by coupling with diazonium
salts.[3] Sudan dyes I–IV and Sudan Red G
consist of arylazo-substituted naphthols.

Selected 2-Naphthol-derived dyes

Sudan I

Sudan II
Sudan III

Sudan IV
Oil Red O

Naphthol AS
Reactions
Some reactions of 2-naphthol are
explicable with reference to its
tautomerism, which produces a small
amount of the keto tautomer.

Tautomeric equilibrium for beta-naphthol

One consequence of this tautomerism is

the Bucherer reaction, the ammonolysis of
2-naphthol to give 2-aminonaphthalene.
2-Naphthol can be oxidatively coupled to
form BINOL, a C2-symmetric ligand
popularized for use in asymmetric
catalysis.

2-Naphthol converts to 2-naphthalenethiol

by reaction with dimethylthiocarbamoyl
chloride via the Newman–Kwart
rearrangement.[4] The OH→Br conversion
has been described.[5]

Electrophilic attack occurs

characteristically at the 1-position as
indicated by nitrosylation[6] bromination,[7]
and alkylations.[8] Ring-opening reactions
have been documented.[9]

Safety
Naphthols (both the 1- and 2- isomers) are
used as biomarkers for livestock and
humans exposed to polycyclic aromatic
hydrocarbons.[10]

References
1. "MSDS safety data for 2-naphthol" (https://
web.archive.org/web/20110303133020/htt
ps://msds.chem.ox.ac.uk/NA/2-naphthol.ht
ml) . Archived from the original (https://ms
 ds.chem.ox.ac.uk/NA/2-naphthol.html) on
3 March 2011.
2. Booth, Gerald (2005). "Naphthalene
Derivatives". Ullmann's Encyclopedia of
Industrial Chemistry. Weinheim: Wiley-VCH.
doi:10.1002/14356007.a17_009 (https://do
i.org/10.1002%2F14356007.a17_009) ..
full-text PDF (https://pdfslide.net/documen
ts/ullmanns-encyclopedia-of-industrial-che
mistry-naphthalene-derivatives.html)
3. Booth, Gerald; Zollinger, Heinrich; McLaren,
Keith; Sharples, William G.; Westwell, Alan
(2000). "Dyes, General Survey". Ullmann's
Encyclopedia of Industrial Chemistry.
Wiley-VCH.
doi:10.1002/14356007.a09_073 (https://do
 i.org/10.1002%2F14356007.a09_073) .
ISBN 9783527306732.
4. Melvin S. Newman; Frederick W. Hetzel
(1971). "Thiophenols from Phenols: 2-
Naphthalenethiol" (https://www.orgsyn.org/
demo.aspx?prep=CV6P0824) . Organic
Syntheses. 51: 139.
doi:10.15227/orgsyn.051.0139 (https://doi.
org/10.15227%2Forgsyn.051.0139) .
5. J. P. Schaefer, Jerry Higgins, and P. K.
Shenoy (1969). "2-Bromonaphthalene".
Organic Syntheses. 49: 6.
doi:10.15227/orgsyn.049.0006 (https://doi.
org/10.15227%2Forgsyn.049.0006) .
6. "Nitroso-β-Naphthol C. S. Marvel and P. K.
Porter". Organic Syntheses. 2: 61. 1922.
 doi:10.15227/orgsyn.002.0061 (https://doi.
org/10.15227%2Forgsyn.002.0061) .
7. C. Frederick Koelsch (1940). "6-Bromo-2-
Naphthol". Organic Syntheses. 20: 18.
doi:10.15227/orgsyn.020.0018 (https://doi.
org/10.15227%2Forgsyn.020.0018) .
8. Alfred Russell Luther B. Lockhart (1942).
"2-Hydroxy-1-Naphthaldehyde". Organic
Syntheses. 22: 63.
doi:10.15227/orgsyn.022.0063 (https://doi.
org/10.15227%2Forgsyn.022.0063) .
9. G. A. Page, D. S. Tarbell (1954). "β-(o-
Carboxyphenyl)propionic Acid". Organic
Syntheses. 34: 8.
doi:10.15227/orgsyn.034.0008 (https://doi.
org/10.15227%2Forgsyn.034.0008) .
10. Sreekanth, R.; Prasanthkumar, Kavanal P.;
Sunil Paul, M. M.; Aravind, Usha K.;
Aravindakumar, C. T. (7 November 2013).
"Oxidation Reactions of 1- and 2-Naphthols:
An Experimental and Theoretical Study" (htt
ps://pubmed.ncbi.nlm.nih.gov/24093754) .
The Journal of Physical Chemistry A. 117
(44): 11261–11270.
Bibcode:2013JPCA..11711261S (https://ui.
adsabs.harvard.edu/abs/2013JPCA..11711
261S) . doi:10.1021/jp4081355 (https://do
i.org/10.1021%2Fjp4081355) .
PMID 24093754 (https://pubmed.ncbi.nlm.
nih.gov/24093754) .
External links
एनआईएसटी के मिस्ट्री वेबबुक 2-नेफ़थलेनॉल (htt
p://webbook.nist.gov/cgi/cbook.cgi?Na
me=2-naphthol&Units=SI)

Retrieved from
"https://en.wikipedia.org/w/index.php?title=2-
Naphthol&oldid=1139396738"

This page was last edited on 14 February 2023, at

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